Norman Spector is Canada's former ambassador to Israel. He was also the publisher of the Jerusalem Post. Conversations about Israel-Palestine are invariably bummers, but for Norman, Jesse makes an exception.

Cartoonist Kate Beaton is an exemplary weirdo. Her webcomic about Canadian historical figures and literary ephemera has gained a global following of one million monthly readers. She has published an acclaimed book and her work appeared in The New Yorker, but she still is largely a self-published online creator. Jesse tries to learn her secrets.